Carbonyl Iron Powder: A Reagent for Nitro Group Reductions under Aqueous Micellar Catalysis Conditions

Abstract

An especially mild, safe, efficient, and environmentally responsible reduction of aromatic and heteroaromatic nitro-group-containing educts is reported that utilizes very inexpensive carbonyl iron powder (CIP), a highly active commercial grade of iron powder. These reductions are conducted in the presence of nanomicelles composed of TPGS-750-M in water, a recyclable aqueous micellar reaction medium. This new technology also shows broad scope and scalability and presents opportunities for multistep one-pot sequences involving this reducing agent.

Coolade. A Low‐Foaming Surfactant for Organic Synthesis in Water

“…(α)‐ N 1 ‐[1‐(4‐methoxyphenyl)ethyl]benzene‐1,4‐diamine ( 6 ): Synthesis was performed according to the procedure described in section 4.1 (procedure B; Supporting Information) using THF cosolvent (25 vol %) and 5 equiv NaBH 4 to give 6 as a yellow oil. Spectroscopic data matched that reported in the literature . R f =0.30 (EtOAc/hexanes 40:60).…”

“…Spectroscopic data matched that reported in the literature. [14] R f = 0.30 (EtOAc/ hexanes 40:60). 1 HNMR (500 MHz, CDCl 3 ): d = 7.32-7.27 (m, 2H), 6.89-6.84 (m, 2H), 6.53 (d, J = 8.6 Hz, 2H), 6.43 (d, J = 8.6 Hz, 2H), 4.37 (q, J = 6.6 Hz, 1H), 3.79 (s, 3H), 3.37 (s, 3H), 1.48 ppm (d, J = 6.7 Hz, 3H); 13 CNMR (126 MHz, CDCl 3 ): d = 158.…”

“…Spectroscopic data matched that reported in the literature. [14] 47,132.12,116.84,110.33,benzyl}oxy]aniline (9): Synthesis was performed according to the procedure described in section 4.1 (procedure B; Supporting Information) using DCM cosolvent (10 vol %) and 5equiv of NaBH 4 to give 9 as ap ale yellow solid. Spectroscopic data matched that reported in the literature.…”

BF3·SMe2 for Thiomethylation, Nitro Reduction and Tandem Reduction/SMe Insertion of Nitrogen Heterocycles

“…6‐Chloropyridin‐3‐amine (6a): light brown solid (19 mg, 30 %) 1 H NMR (400 MHz, CDCl 3 ) δ 3.67 (bs, 2H, N H 2 ), 6.95 (dd, J = 8.5, 3.0 Hz, 1H, Ar H ), 7.07 (d, J = 8.5 Hz, 1H, Ar H ), 7.84 (d, J = 3.0 Hz, 1H, Ar H ). 13 C NMR (101 MHz, CDCl 3 ) δ 124.3, 125.0, 136.4, 140.3, 141.8.…”

CO-free, aqueous mediated, instant and selective reduction of nitrobenzeneviarobustly stable chalcogen stabilised iron carbonyl clusters (Fe3E2(CO)9, E = S, Se, Te)

“…34 Recently in 2017, Lipshutz and co-workers used carbonyl iron powder under aqueous micellar catalysis condition. 35 Fe(CO) 5 and Fe 3 (CO) 12 have also been used for nitro reduction, but all the methods require rather drastic reaction condition, including long duration, high pressure of CO gas, handling of highly toxic Fe(CO) 5 , reducing agent and various supporting reagents for to promote the reaction. 36 Recently, chalcogen and metal chalcogenide complexes have come under the spotlight, these complexes are continuously breaking the stereotype of air and moisture sensitive metal complexes.…”